Reactions of azoalkenes derived from hydrazones of ethyl bromopyruvate with electron rich alkenes and heterocycles

Three hydrazones of ethyl bromopyruvate, the dinitrophenylhydrazone 2a, the toluene-4-sulphonylhydrazone 2b and the t-butoxycarbonylhydrazone 2c, have been reacted with a series of nucleophilic alkenes and heterocycles in the presence of sodium carbonate. Azoalkenes 3 are presumed as intermediates a...

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Detalhes bibliográficos
Autor principal: Clarke, S (author)
Outros Autores: Gilchrist, Thomas L. (author), Lemos, A. (author), Roberts, Tony G. (author)
Formato: article
Idioma:eng
Publicado em: 2012
Assuntos:
Texto completo:http://hdl.handle.net/10400.1/934
País:Portugal
Oai:oai:sapientia.ualg.pt:10400.1/934
Descrição
Resumo:Three hydrazones of ethyl bromopyruvate, the dinitrophenylhydrazone 2a, the toluene-4-sulphonylhydrazone 2b and the t-butoxycarbonylhydrazone 2c, have been reacted with a series of nucleophilic alkenes and heterocycles in the presence of sodium carbonate. Azoalkenes 3 are presumed as intermediates and adducts have been isolated. The azoalkenes derived from hydrazones 2a and 2c are found to be useful electrophiles and electrophilic dienes.